Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid

被引：315

作者：

Cowen, Bryan J. ^{[1
]}

Miller, Scott J. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 36期

关键词：

D O I：

10.1021/ja0734243

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric [3 + 2]-cycloaddition reactions between CC-allenic esters and enones are presented. We have found that a simple phosphine-containing protected (X-amino acid derivative is capable of promoting such cycloadditions in high yields with significant levels of regioselectivity and enantioselectivity. Furthermore, employing chiral racemic gamma-substituted allenoates in the cycloaddition with chalcone substrates results in a "deracemization" reaction furnishing cyclopentenes in high yields with up to 93% ee.

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页码：10988 / +

页数：3

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